Well, in mountainbike terms, the Lefty was lighter and stronger (but a lot more expensive) than a comparable 140mm fork. They also suffered a lot less from 'stiction' than conventional forks.
It's probably just Cannondale being innovative/different for the sake of it, but it's great for changing tubes/tyres without having to remove the front wheel. That may be a benefit to a road rider too. I'm not sure one way or the other about the weight of the ones designed for road use, and sure there is an element of cosmetic 'bling' factor too.
As for motorbikes - yes, I think there may well be such a thing as 'too stiff' when you're talking about Rossi and the like. I believe the single sided swingarms are a bit heavier. I've always liked the look of them though - Daytona 955, VFR, and of course the legendary NR750... bike porn!